There’s a famous story about early movie mogul Harry Cohn. He founded Columbia Pictures back in the silent era and ran it well into film’s heyday. He said he could judge how good or bad a movie was by whether his fanny started to squirm while watching. It prompted the startling rejoinder from writer Herman J. Mankiewicz: “Imagine, the whole world wired to Harry Cohn’s ass.”
I often think music execs have a similar system for judging whether a particular song has overstayed its welcome. Pop songs evolved into their standard lengths in part due to radio programming requirements and in part due to how much would fit on a 45. But there was an organic evolution as well. Three or four minutes just kind of felt right to a lot of people. By that point, they were ready for a new melody.
We’ve been running through a sampling of longer songs that dared to challenge the norms of run time. They branched out with more involved compositions and more developed lyrical content. The ones we have been looking at in our two previous journeys doubled and sometimes tripled standard lengths. So far, we have looked at songs that ran between eight and fourteen minutes. Today, we soar past fourteen into the really long songs that have still found their way onto popular music releases.
Five long songs whose every second is priceless
The early zenith of this exploration occurred in 1972 when Jethro Tull’s Ian Anderson produced his response to “concept albums,” Thick as a Brick. One song ran for almost 44 minutes. It had to be split into two sections for inclusion on an LP. I’m not including “Thick as a Brick,” (the song – not the album) because I don’t especially like it. Or, more accurately, because I really do like pieces of it and think Anderson did the overall piece of music a disservice by forcing it to adhere to his preconception of having one album-length song. In other words, this is a case where I do not listen the ”Thick as a Brick” precisely because it is too long.
So I am in fact choosing shorter songs. But they are songs I very much enjoy sitting down and listening to all the way through. They run the gamut from sophisticated musical compositions to a tidal wave of poetry (the kind you might expect from a Nobel Laureate in literature.) There are smoking guitar raves, both of the jazz and the punk variety. And there is one epic from one of the most vital voices in rock & roll in the 21st century.
To borrow from Blue Oyster Cult, don’t fear the time span...
“TELEGRAPH ROAD” by Dire Straits – 1982 (14:18)
“Telegraph Road” came from Love Over Gold, either Mark Knopfler’s most ambitious album, or his most pretentious. Most critics admired the long, complex song structures. But Robert Christgau called it “pompous,” and served up what from him was extreme putdown – “ELP with blues roots.”
Christgau is a crucial figure in rock & roll criticism, but he missed the boat here. That’s not to say Love Over Gold avoids all pomposity. It doesn’t. But its magnum opus, “Telegraph Road” earns its length.
A slow, atmospheric siren gives way to rumblings and primordial explosions before a piano and guitar begin to carve out the basic melody line. About two minutes in, Knopfler’s voice begins the story, and it is some of his best, most efficient writing. It has to be, as it attempts to cover a large swath of societal evolution in a few verses. “Then came the churches, then came the schools – Then came the lawyers, then came the rules – Then came the trains and the trucks with their load – And the dirty old track – Was the Telegraph Road.”
A little past the five-minute mark, Knopfler might have been done, He had a complete story. But he chooses to make the history more immediate by bringing it right up to date with a personal story of a modern automaton spawned by the Telegraph Road world. That second stretch carries us to the ten-minute mark. Then it’s all Knopfler and his virtuoso finger-picking building to a titanic conclusion.
“VOODOO CHILE” by Jimi Hendrix – 1968 (14:50)
Jimi Hendrix began his final studio album, the monumental Electric Ladyland, with a short noisy track, followed by a gorgeous short composition referencing the album’s title. And a raver called “Crosstown Traffic.” Together, the three songs run under six minutes. Then he concludes side 1 with the ultimate jam – “Voodoo Chile.” He had his drummer, the sensational Mitch Miller with him, along with the bass player from Jefferson Airplane, Jack Casady, and a 20-year kid on keyboards named Stevie Winwood. They decided to play a little Muddy Waters.
Fifteen minutes later, they had one of the greatest studio jams ever captured on tape. Hendrix is restrained early on, allowing Winwood to run wild on his Hammond organ. But it doesn’t take long before Jimi’s guitar and Mitch’s drums join the free-form exploration. All the while, Casady’s bass keeps the pace.
Right in the middle, you think it might be over. There is even a smattering of applause. But these guys are just getting warmed up. The band members trade off little solo runs throughout the second half, with Jimi’s guitar usually the brightest bulb in the room. Even if you’re not looking to chill out, or seeking out a heavy dose of jazz fusion, there’s something undeniably hypnotic about the way Jimi Hendrix sells a song.
Later, Jimi, Mitch, and Experience bassist Noel Redding would adapt the long jam into a five-minute single called “Voodoo Child (Slight Return).” It is shorter, tighter, and less languid than the long jam should you have a little less time, or need a little more high octane in your tank.
“MURDER MOST FOUL” by Bob Dylan – 2020 (16:54)
Bob Dylan was among the first popular singer/songwriters to seriously stretch the length of the modern popular song. At almost seven minutes, “A Hard Rain’s a-Gonna Fall” was revelatory back in 1963. That was just his second album, released just after his 22nd birthday. He went over seven minutes on his next album, and he would continue mixing long songs into his albums over the next several years. It seemed he had reached a peak with “Sad Eyed Lady of the Lowlands,” the gorgeous finale to his double album Blonde on Blonde in 1966. It ran over eleven minutes.
Then, more than fifty years later, he closed his 39th studio album Rough and Rowdy Ways with an expansive examination of one of the most formative events of his life – the assassination of John Kennedy. Emerging slowly from a triple-keyboard attack, Dylan’s visceral writing is on full display: “President Kennedy was riding high – Good day to be living and a good day to die.” He tells the story of the assassination in an efficient two minutes.
And then he invokes Wolfman Jack. I can’t think of any other songwriter who would have made that connection, but in Dylan’s voice, it works. It gives him a conduit into the American culture before, during and after the shot that to a great many Americans, changed the trajectory of a nation. The references are too plentiful to cite here, and there have been countless detailed analyses of the lyrics and the cultural touchstones. There will be countless more to come.
I’ll just close by pointing out that this is not a poem. It is a song, and Dylan, though never an accomplished musician, understood how to use music to frame his stories as well as any songwriter ever has. These seventeen minutes do not work if all those words are not floating along a river of all-encompassing, elegiac music. The words make you think. The music makes you cry. It’s well worth the time invested.
“SISTER RAY,” by The Velvet Underground – 1968 (17:31)
On the debut VU album, Lou Reed and his bandmates rewrote the rules for pop song subject matter. On the follow-up White Light/White Heat, they went even further. At over 17 minutes, the final track, “Sister Ray,” is among the longest songs on any rock & roll album of the 1960s.
But the sheer length is only one of the revolutionary aspects of “Sister Ray.” From the opening loud, sludgy guitar and organ, we are immediately in a different world. Pretty soon, we are searching for our mainline – and could not hit it sideways. This is Reed’s way of telling us the characters in this story are stoned out of their minds.
We get fleeting glimpses of characters in “Sister Ray,” – like the wild orgy Randy Newman would visit in “Mams Told Me Not to Come.” But the cacophony of Reed and fellow guitarist Sterling Morrison provide an insistent nightmare from which we cannot escape. John Cale’s bass rambles all over the place, while his organ butts heads with those guitars. And beneath it all, Maureen Tucker’s drums, which feel like they might be coming from the studio down the hall, relentlessly bang ahead barely keeping the volatile mix in check.
Word is that the support staff working with VU on the recording were so bewildered, distracted, and maddened by the waves of sound they were trying to capture and modulate that they didn’t even mic Tucker’s drums properly, which explains their distance. If you care to, you can hear the story of stoned drag queens and murder that just gets washed away in the rawness of the sound. Punk rock – as a genre – may have been birthed before this, but this song is the wellspring. Anyone who set out to make loud, fast noise with a guitar can trace their musical DNA back to “Sister Ray.”
“THE DECLINE,” by NOFX – 1999 (18:20)
Green Day released American Idiot in 2004 to rave reviews. It was the fullest rumination that punk rock had produced about the modern decline of the American Dream. The previous title holder was Fat Mike and NOFX’s EP “The Decline” which is arguably tighter and more succinct, even at more than 18 minutes. “The Decline” is a single EP-length song that describes the dumbing down of American culture, and to tell the story, Fat Mike returned to the early pop punk (or melodic hardcore if you prefer) sounds that won NOFX a wide audience a decade earlier.
He set out to write an epic. "Where are all the stupid people from -- And how did they get so dumb?" Those are his opening questions. Like Lou Reed, he was marshaling many of the stories he had heard and seen during his time touring the land and writing them into a multi-part novel. And there was a ferocity to the righteous anger. The blistering music matched his words.
The lyrics are not funny – Fat Mike is not hiding his brutal observations behind humor as many punk writers might. But they are witty. "Bred on purple mountain range -- Feed amber waves of grain -- To lesser human beings -- Zero feelings." There are tempo changes. There are micing shifts. The song lurches and careens like a misfiring engine, but it never gives out or even really slows down. The effect is to keep you engaged through sheer nervous energy.
There are short songs and long songs that strike a chord when they are released but seem to date poorly over time. “The Decline” has grown. It is prophetic. Its music still feels fresh. And I think that is true of all of the songs on this list. I mean, if you’re really going to risk having your record label’s boss man’s fanny start squirming through a song that runs well past four minutes, you better have something to say. And the sounds to make us listen. And the sheer audacity to travel to places few other artists care to go.

